Lubricant composition



Patented Mar. 14, 1950 LUBRICANT COMPOSITION William E. Garwood,Haddonfield, Francis M. Seger, Pitman, and Alexander N. Sachanen,Woodbury, N.,J., assignors to Socony-Vacuum Oil Company, Incorporated, acorporation of New York No Drawing. Application June 16, 1948,

- Serial No. 33,438

17 Claims. 1

This invention has to do with the condensation or normal alp 'iamono-olefins, certain conjugated hydrocarbons and sulfur, andparticularly has to do with the new and useful compositions obtained bysaid condensation.

As is well known to those familiar with the art, olefins have previouslybeen polymerized. So also have conjugated hydrocarbons. Each of theseunsaturated materials has previously been reacted individually withsulfur, and olefins and conjugated hydrocarbons have previously beenreacted together. In the latter instance, copolymerizationis generallyincomplete. For example, when decene-l and styrene are copolymerized at600 R, an oil containing a polystyrene cloud at room temperature (20-25C.) is formed. In no known instance, however, have alpha-normalmono-olefins been condensed with conjugated hydrocarbons, of thecharacter defined hereinbelow, and sulfur.

It has now been discovered that normal alpha mono-olefins condense withcertain conjugated hydrocarbons and sulfur, under conditions hereinafterdefined, with the formation of highly desirable viscous oils. The oilsso formed are free from the shortcomings of olefin-conjugatedhydrocarbon copolymers, as illustrated by the styrene-decene-l copolymerreferred to above. Further, the viscous oils of this invention areunusually stable. Catalytic oxidation stability tests demonstrate themto be superior to condensation products of decene-l alone, and superiortocondensation products of decene-l and styrene. The characteristics ofthe new oils are such as to make them outstanding synthetic lubricatingoils, for use alone or blended with other lubricants.

REACTAN TS As indicated above, the mono-olefin reactants of thisinvention are normal or straight chain alpha mono-olefins and containfrom 5 to 18 carbon atoms. Such mono-olefins are normally liquid attemperatures of the order of 20-25 C. Illustrative of such mono-olefinsare the following: pentene-l, octene-l, decene-l, dodecene-l,

octadece e-l, and the like. Preferred, however, of such lefins are thosehaving from 8 to 12 carbon atoms, with decene-l representing aparticularly desirable olefin. It will be clear from the foregoingexamples that an alpha olefin may also be referred to as a l-olefin.

Not only may the mono-olefins of the aforesaid character be usedindividually in this invention, but they may also be used in admixturewith each other. In addition, olefin mixtures containing a substantialproportion of such mono-olefins may be used. Preferred of such mixturesare those containing a major proportion of a l-olefln or of l-olefins.Rrepresentative of such mixtures are those obtained by the cracking ofparaffln waxes and other paraffin products; those obtained from theFischer-Tripsch and related processes.

These hydrocrabon mixtures may contain, in addition to the l-olefin orl-olefins, such materials as: other olefins, parafiins, naphthenes andaromatics.

The conjugated reactants contemplated herein are conjugated hydrocarbonsand derivatives thereof, wherein the conjugated system is represented bythe grouping:

Of such conjugated hydrocarbons, butadiene and styrene have been foundto be particularly desirable for the purposes of this invention. Theseconjugated hydrocarbons are characterized by at least one vinyl group,

in a 1:3 conjugated relationship with another double bond. Furtherexamples of such conjugated hydrocarbons are: isoprene (Z-methylbutadiene), l-phenyl butadiene, divinyl benzene, vinyl naphthalene, andthe like. Inasmuch as other conjugated hydrocarbons form polymericmaterials, as illustrated by cyclopentadiene, methyl isoprene, and thelike, such hydrocarbons may also be used to form satisfactory productswith the aforesaid l-mono-olefin and sulfur. It will be noted that allof the foregoing conjugated materials are hydrocarbons.

Derivatives of the conjugated hydrocarbons, or substituted conjugatedhydrocarbons, which typify those contemplated herein are:halogen-substituted materials such as chloroprene (2-chlorobutadiene),l-bromo butadiene and p-chlorostyrene; alkoxy-substituted materials suchas p.-

methoxy styrene; etc. As will be noted from the character of theforegoing typical substituted conjugated hydrocarbons, substituentgroups which may be present are those which do not interfere with thecourse of the condensation of the conjugated system with the aforesaidalphamono-olefln and sulfur. In other words, a substituent group whichmay be present on the conjugated hydrocarbon is one which issubstantially inert or unreactive in the condensation. The substituentgroup, however, generally modihes the character of the oil product; yet,in all cases, the products are characterized by unusual stability andare useful as lubricants. For example, when chloroprene or p-chlorostyrene is used, the synthetic lubricant formed is also characterized byextreme pressure properties.

In connection with divinyl benzene, which may be used as a conjugatedreactant, it should be noted that this reactant is characterized by ahigh degree of reactivity in view of the two vinyl groups. For mostsatisfactory results with divinyl benzene, a relatively small quantityshould be used with a l-mono olefin and sulfur. Accordingly, in thediscussion of reaction proportions hereinafter, it should be recognizedthat the quantity of divinyl benzene used will generally be at the lowerend of the conjugated reactant proportion range.

It will be understood, of course, that mixtures of the aforesaidconjugated hydrocarbons, and their aforesaid derivatives, may be used inplace of the individual reactant. Similarly, mixtures containingsubstantial, and preferably major, proportions of one or more of saidconjugated reactants may be used. Examples of such mixtures are: acrude-styrene containing ethyl benzene, a crude butadiene containingbutenes, and coal tar light oils which contain dicyclopentadiene,indene, coumarone, and aromatics.

As will be evident from the foregoing discussion of the conjugatedreactant, benzene is not considered herein as a conjugated hydrocarbon,despite its alternate double bond character. In contrast with benzene,the conjugated reactants, as aforesaid, are characterized by at leastone vinyl 8 9 in a 1:3 conjugated relationshi with another double bond.

Preferred of the conjugated reactants are those having only oneconjugated grouping with particular preference being given to styreneand butadiene.

As indicated above, sulfur is condensed with the alpha mono-oleflns andconjugated reactants defined above. Also contemplated herein for suchcondensation in place of sulfur are selenium and tellurium. The lattermay replace sulfur in part or in entirety, and mixtures of two or allthree of said substances may be used. In view of the availability andlow cost of sulfur, and in view of the outstanding character of the oilsobtained therewith, sulfur is particularly preferred herein. It is onthis basis that the following discussion and illustrative examples aredirected to oondensatlons involving sulfur.

REACTION CONDITIONS Condensation of the aforesaid reactants is affectedat elevated temperatures. It appears that temperatures as low as 300 F.and as high as- 900" F. can be used in some instances; however,temperatures of the order of about 400 F. to about 750 F. are mostsatisfactory. The preferred temperature range is from about 600 F. toabout 650 F.

Condensation is generally complete in from 1 to 10 hours, with thehigher reaction temperatures being used for the shorter reactionperiods. and with the lower reaction temperatures being used for thelonger reaction periods.

Pressures ranging from atmospheric to 4000 pounds per square inch may beused. In general, it is desirable to use suillcient pressure to maintainthe reactants in liquid state.

Proportions of reactants can be varied considerably. With one molarproportion of an alpha mono-olefin as the basis, from about 0.01 toabout 1 molar proportion of conjugated reactant and from about 0.001 toabout 1 molar proportion of sulfur, provide satisfactory products.Preferred proportions, however, are from about 0.05 to about 0.5 molarproportion of conjugated reactant and from about 0.01 to about 0.5 molarproportion of sulfur, with one molar proportion of alpha mono-olefin.

It will be understood, of course, that the condensation is aided byproviding mixing of the reactants. This may be provided b using variousagitating means which are well known in the art. At the reactionconditions, the reactants are mutually soluble and homogeneity is easilyattained.

- EXAMPLES In order to illustrate the principles of this invention, theresults of a series of typical, and nonlimiting, condensations are setforth in tabular form in Table I below. These condensations were carriedout in a rocking-type bomb (American Instrument Co.). The reactants werecharged to the bomb, which was then heated to the desired temperaturefor the desired length of time. Thereafter, the bomb was cooled, anddischarged. The contents of the bomb were vacuum distilled to removeunreacted materials. It should be noted that the reaction times, recitedas Time. hours" in Table I, represent the time intervals during whichthe bomb was maintained at the desired temperature, and do not includethe time intervals necessary to heat the bomb and its contents to thedesired temperature, and do not include the time intervals necessary tocool the bomb after heat to the bomb has been discontinued.

The condensation products discharged from the bomb, or other reactionvessel, were distilled and filtered, as in the runs shown in Table I. Todistinguish the condensation products from the distillate fractionsthereof, the refined oils are identified as residual oils. The latterterm identifles the oils from which unreacted materials and products ofintermediate boiling range have been separated.

All the tests and analyses to which the residual oils in Table I weresubjected are well known standard'tests. In this connection, it will benoted that the designation N. N." refers to the neutralization number,which is a measure of the acidity of the oil.

- Styrene used in these condensations contained a fract on of one percent of p-tertiary-butyl catechol, the latter acting as a stabilizer orpolymerization inhibitor. This styrene material is the commercialproduct now available.

. um I Cmldenaattcm of olefin: with sulfur and conluaated hydrocarbonsRun l 2 3 4 5 0 7 Olefin Deanne-1.. Dooene-L. Decene-L. Decene-lDecline-1.. Decene-L. Deoene-l.

Styrene. Styrene Styrene. 78 26 26.

Mex. Pressure p. e. i. g

Diltlllation 0! Reaction Product:

Mlmvaportem .,"C Pressure, mm.

Residual Oils:

Grams Cloud at Room Temp. (22 0.) gle U. at 210 F 1 Your, '1".. Br.Addn. Refractive Index. S \eciilo Gravitym. 2 .5 0. eroent S 2.57 3.260.23 0.85. Distillate, Br No- 87.B 109.23...." 87.0 99.3. ercen 0.930059..--.- 0.12.

Decene-L. Decene-l 280.- 366.

G Cloudy at Room Temp. (22 0.). 8. U. at 210 F Br. Addn RefractiveIndex.

2.0. Styrene. 28

2.0: Styrene. 62

1 292 3. reaction product irom bomb first heated at atmospheric pressureto maximum liquid temperature of 180 0., no distillate.

I Some reaction product lost from bomb. I Adsorbont clay used to improvecolor, with large loss. Color (Lovibond) carbon residue (Ramsbottom)-0.1.

As can be seen from the data set forth in Table I, above, the omissionof sulfur in run-2 resulted in the formation of a resin, and in run 5resulted in the formation of a product that was cloudy at roomtemperature (22 C.). In the latter case, the cloud point was actuallyF., in contrast to cloud points of less than 34 F. for the comparableproducts of run-6 and run-8.

Evidence that styrene condensed with decene- 1 and sulfur in run-8 isshown by infra-red analysis of the residual oil. Such analysis clearlyindicated the presence of aromatic rings in the residual 011. Additionalevidence is shown by chemical analysis of the residual oil, the lattercontaining 0.81 per cent sulfur, 85.99 per cent carbon and 13.11- percent hydrogen. This anal ysis indicates that the residual oil iscomposed of 0.81% sulfur, 16.3% reacted styrene (as compared with 8.4%monomer in the charge mixture) and 82.9% reacted decene-l (as comparedwith 90.9% monomer in the charge mixture).

, rosive sulfur, the latter often being present as loosely-bound sulfurin an oil. In this test, 50 mls. of the oil to be tested are placed in amls. beaker along with a polished copper strip, about /2 inch by 2inches. The copper strip is bent into a V and so placed in the beakerthat th flat surface thereof does-not touch the bottom or sides of thebeaker. The oil sample in the beaker completely covers the copper strip.The beaker, containing oil sample and copper strip, is placed in anelectric oven for the required period of time. Thereafter, the beaker isremoved from the oven and the copper strip is removed from the beaker.The strip is washed with petroleum ether and then is examined forcorrosion. After 26 hours at 100 C., the copper strip subjected to theresidual oil from run- 13 was only slightly stained and the oil had onlyslightly darkened. There was no sludge in the oil sample. This test,then, demonstrates that the sulfur present in the oil is firmly boundand that no free sulfur is present in the oil. It will be noted in TableI, above, that the residual oil from run-13 contains 0.62 percentsulfur.

The stability of the oils of this invention is revealed by the resultsof a. catalytic oxidation test, to which were subjected several of theresidual oils shown in Table I, above. In this test 6.5 feet of No. 14(Brown and Sharpe gauge) iron wire (15.6 square inch), 6.2 inches of No.18 (B. I: 8). copper wire (0.78 square inch), 3.33 inches of No. 12 (B.8: S.) aluminum wire (0.87 square inch), a $4 inch square of inch leadsheet (1% square inch), and 25 ccs. of the test 011 were placed in aglass test tube, heated to 260 F. and air blown therethrough at the rateof liters per hour for 40 hours.

Changes in the characteristics of the oil, sludge formed, and efiects ofoil on the copper coil and on the lead sheet were reported. on the basisof these changes, the residual oils were rated as compared with a SAE-IOsolvent refined Pennsylvania motor oil subjected to the same test. Theresults of these tests and of the comparisons obtained in run-13, of.Table I, above, was sub-.

jected to a Lauson oxidation stability test. In this test, a Lausonsingle cylinder, four-cycle gasoline engine is used. The engine hassplash lubrication and a copper-lead bearing. It is operated with an oiltemperature of 270 F. and a jacket temperature of 212 F., and a speed of1825 revolutions per minute (R. P. M.). In the test, the engine is runat one-half throttle, with a 13.0-1 air-fuel ratio. The engine isinspected every hours, with hearing weight loss, engine cleanliness andused oil analyses being reported.

The results of the aforesaid Lauson test are presented in Table IIIbelow. In this table, a comparison is shown of R-13 residual oil. and ofa blank, an SAE-20 grade Pennsylvania mineral oil which is predominantlyparaflinic in character.

TABLE III Lauson OS-Z engine test on sunthetieoil from de cane-1 styreneand sulfur Bearlilggslvgeight Rating Viscosity Insol. in Insol. in OilHours N. N. 210 ANS. gt M Otnloro- 1 cs. an t a orm Ovcral Top 2: Clean-Dem liness gency Blank 20 2.2 9. 74 40 4.1 11.00 5.2 11.76 5.3 12.13 5.212.00 R-l3 0 0. 2 1 4. 60 20 1.0 v 4.90 40 1.0 5.11 60 2.3 5. 25 80 2.65.88 100 2. 5 l 5. 45

1 Viscosity index-120.9, pour point20 F. I Viscosity index-120.3, pourpoint=25 F.

with SAE-IO Pennsylvania motor oil are reported in Table II below.

TABLE II Catalytic oxidation test .Run

Time, Hours Sludge Tube Copper Coil Load L05, Mgm Rated Against NilEqual"...

Worse Equal...

1 Indicates oil is very bad in this factor and would probably fail in anengine test.

From inspection of the results shown above in Table II, it will be seenthat in every instance the new synthetic oils are equal to or betterthan SAE-IO Pennsylvania motor oil in every less for the residual 011,59-13, than for the blank oil. The average loss for the top and bottomsections of the bearing in contact with the blank oil is 0.491 gram, ascompared with only 0.085 gram when the oil is 12-13 residual oil.Consistent with this comparison is the large differences in N.N. valuesfor the two oils. While the engine cleanliness rating for R-13 residualoil is somewhat lower than the rating for the blank oil, it is of thesame order as the blank oil when the latter contains a small amount of aconventional antioxidant (which tends to make for lowered cleanlinessrating). The blank oil requires such an anti- 1 oxidant to preventbearing loss and thus meet present day lubricant requirements. It willalso be noted that the viscosity change of 12-13 residual oil over the100 hour period is only 18 per cent, as against a 23 per cent change forthe blank oil. Finally, it should be noted that R 13 residual oil has alow initial pour point, 20 F., and at the end of the test still has alow pour point, -25 F. This demonstrates that the oil does not undergoreversion of pour point, which is a serious problem today with oils'ofthe type of the blank, particularly when the latter contains certain ofthe commercially available pour point depressants.

As will be evident from the data presented above in Tables I, II andIII, the condensation products of this invention are highly desirablelubricants per se. They are also of considerable value as blendingagents for other lubricating oils. In view of the inherent stability ofthe synthetic oils, they impart stability to the oils with which theyare blended. So also, they impart desirable viscosity index (V. I.) andpour point characteristics to the oils in combination therewith, for, asindicated above, they have advantageous vis cosity index and pour pointproperties. In short, the synthetic oils find utility in upgrading otherlubricants. Typical oils with which the synthetic oils may be blendedare mineral oils such as are normally used in internal combustion andturbine engines. When so blended, the synthetic oils may comprise themajor proportion of the final blended oil, or may even comprise a minorproportion thereof. For example,

although used only in the amounts of the order of 1 to per cent, thesynthetic oils improve the stability of mineral oils, such as SAE 10 and20 Pennsylvania type oils.

One or more of the individual properties of the synthetic lubricants ofthis invention may be further improved by incorporating therewith asmall, but effective amount, of an addition agent such as a detergent,an extreme pressure agent, a foam suppressor, a viscosity index (V. I.)improver, etc. Typical detergents which may be so used are metal saltsof alkyl-substituted aromatic sulfonic or carboxylic acids, asillustrated by diwax benzene barium sulfonate' and barium phenate,barium carboxylate of a wax-substituted phenol carboxylic acid. Extremepressure agents are well known; illustrating such materials are numerouschlorine and/or sulfur containing compositions, one such material beinga chlornaphtha xanthate. Silicones, such as dimethyl silicone, may beused to illustrate foam suppressing compositions. Viscosity indeximproving agents which may be used are typified by polypropylenes,polyisobutylenes, polyacrylate esters, and the like.

contemplated also as within the scope of this invention is a method oflubricating relatively moving surfaces by maintaining therebetween afilm consisting of any of the aforesaid oils.

It is to be understood that the foregoing description and representativeexamples are nonlimiting and serve to illustrate the invention,

10 which is to be broadly construed in the light of the language of theappended claims.

We claim:

1. The method of preparation of a viscous oil, which comprises:condensing, at a temperature between about 400 F. and about 750 F. for aperiod of time from about ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having from 5 to18 carbon atoms per molecule, from about 0.01 to about one molarproportion of a conjugated -hydrocarbon and from about 0.001 to aboutone molar proportion of a substance selected from the group consistingof sulfur, selenium and tellurium; said conjugated hydrocarbon beingcharacterized by at least one --(.'=c-o=o- I I I I grouping and beingselected from the group consisting of conjugated hydrocarbons andsubstituted conjugated hydrocarbons wherein a substituent is one whichis substantially inert in said condensation.

2. The method of preparation of a viscous oil, which comprises:condensing, at a temperature between about 400 F. and about 750 F. for aperiod of time fromabout ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having from fiveto eighteen carbon atoms per molecule, from about 0.01 to about onemolar proportion of a conjugated hydrocarbon and from about 0.001 toabout one molar proportion of sulfur; said conjugated hydrocarbon beingcharacterized by at least one -o=o-o=c I I I I grouping and consistingessentially of the elements carbon and hydrogen.

3. The method of preparation of a viscous oil, which comprises:condensing at a temperature between about 400' F. and about 750 F. for aperiod of time from about ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having from fiveto eighteen carbon atoms per molecule, from about 0.01 to about onemolar proportion of a substituted conjugated hydrocarbon and from about0.001 to about one molar proportion of sulfur; said conjugatedhydrocarbon being characterized by at least one c=o-o=o I I l I groupingand having a halogen substituent.

4. The method of preparation of a viscous oil, which comprises:condensing, at a temperature between about 400 F. and about 750 F. for aperiod of time from about ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having from fiveto eighteen carbon atoms per molecule, from about 0.01 to about onemolar proportion of a substituted conjugated hydrocarbon and from about0.001 to about one molar proportion of sulfur; said conjugatedhydrocarbon being characterized by at least one c=c-c=o I I I groupingand having an alkoxy substituent.

5. The method of preparation of a viscous oil, which comprises:condensing, at a temperature between about 400 F. and about 750 F. for aperiod of time from about ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having fromeight to twelve carbon atoms per molecule, from about 0.01 to about onemolar proportion of a conjugated hydrocarbon and from about 0.001 toabout one molar proportion of sulfur; said conjugated hydrocarbon beingcharacterized by at least one -c=o-o=e I I I I grouping and consistingessentially of the elements carbon and hydrogen.

6. The method of preparation of a viscous oil, which comprises:condensing, at a temperature between about 400 F. and about 750 F. for aperiod of time from about ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having from fiveto eighteen carbon atoms per molecule, from about 0.01 to about onemolar proportion of a conjugated hydrocarbon and from about 0.001 toabout one molar proportion of sulfur; said conjugated hydrocarbon beingcharacterized by one -c=o-o=c- I I I l grouping and consistingessentially of the elements carbon and hydrogen.

7. The method of preparation of a viscous oil, which comprises:condensing at a temperature between about 600 F. and about 650 F. for aperiod of time from about ten hours to about one hour, respectively, onemolar proportion of a straight chain, alpha mono-olefin having from fiveto eighteen carbon atoms per molecule, from about 0.01 to about onemolar proportion of a conjugated hydrocarbon and from about 0.001 toabout one molar proportion of sulfur; said conjugated hydrocarbon beingcharacterized by at least one -o=c-c=c I l l I grouping and consistingessentially of the elements carbon and hydrogen.

8. The method of preparation of a viscous oil, which comprises:condensing, at a temperature between about 400 1". and about 750 F. fora period of time from about ten hours to about one hour, respectively,one molar proportion of a straight chain, alpha mono-olefin having fromfive to eighteen carbon atomsper molecule, from about 0.05 to about 0.5molar proportion of a conjuagated hydrocarbon, and from about 0.01 toabout 0.5 molar proportion of sulfur; said conjugated hydrocarbon beingcharacterized by one I l I grouping and consisting essentially of theelements carbon and hydrogen.

9. A condensation product obtained by: condensing, at a temperaturebetween about 400 F. and about 750 F. for a period of time from aboutten hours to about one hour, respectively, one molar proportion of astraight chain, alpha mono-olefin having from live to eighteen carbonatoms per molecule, from about 0.01 to about one molar proportion of aconjugated hydrocarbon and from about 0.001 to about one molarproportion of a substance selected from the group consisting of sulfur,selenium and tellurium; said conjugated hydrocarbon being characterizedby at least one I I I I grouping and being selected from the groupconsisting of conjugated hydrocarbons and substi- 12 tuted conjugatedhydrocarbons wherein a substituent is one which is substantially inertin said condensation.

10.A condensation product obtained by: condensing, at a temperaturebetween about 400' F. and about 750 F. for a period of time from aboutten hours to about one hour, respectively, one molar proportion of astraight chain, alpha mono-olefin havingfrom five to eighteen carbonatoms per molecule, from about 0.01 to about one molar proportion of aconjugated hydrocarbon and from about 0.001 to about one molarproportion of sulfur; said conjugated hydrocarbon being characterized byat least one -c=c-c=o- I I I l grouping and consisting essentially ofthe elements carbon and hydrogen.

11. A condensation product obtained by: condensing, at a temperaturebetween about 400 F. and about 750 F. for a period of time from aboutten hours to about one hour, respectively, one molar proportion of astraight chain, alpha mono-olefin having from eight to twelve carbonatoms per molecule, from about 0.01 to about one molar proportion of aconjugated hydro.- carbon and from about 0.001 to about one molarproportion of sulfur; said conjugated hydrocarbon being characterized byat least one C=C Q=C I l I I grouping and consisting essentially of theelements carbon and hydrogen.

12. A condensation product obtained by: condensing, at a temperaturebetween about 400 F. and about 750 F. for a period of time from aboutten hours to about one hour, respectively, one molar proportion of astraight chain, alpha monoolefln having from five to eighteen carbonatoms per molecule, from about 0.01 to about one molar proportion of aconjugated hydrocarbon and from about 0.001 to about one molarproportion of sulfur; said conjugated hydrocarbon being characterized byone grouping and consisting essentially of the elements carbon andhydrogen.

13. A condensation product obtained by: condensing, at a temperaturebetween about 600 1''. and about 650 F. for a period of time from aboutten hours to about one hour, respectively, one molar proportion of astraight chain, alpha monoolefln having from five to eighteen carbonatoms per molecule, from about 0.01 to about one molar proportion of aconjugated hydrocarbon and from about 0.001 to about one molarproportion of sulfur; said conjugated hydrocarbon being characterized byat least one C=Q-C=C I l l I grouping and consisting essentially of theelements carbon and hydrogen.

14. A viscous oil composition comprising a mineral oil of lubricatingviscosity in major proportion and a minor proportion, from about one toabout ten per cent, of a condensation product; said condensation productbeing obtained by: con. densing, at a temperature between about 400 F.and about 750 F. for a period of time from about ten 'hours to about onehour, respectively, one molar proportion of a straight chain, alphamonoolefln having from five to eighteen carbon atoms per molecule, fromabout 0.01 to about one molar four molar proportions of styrene and onemolar proportion of sulfur.

16. A condensation product of lubricating viscosity obtained by:condensing, at a temperature of about 600 F. for about ten hours andwith a pressure of about 250 pounds per square inch, about four molarproportions of decene-l, about one molar proportion of styrene and onemolar proportion of sulfur.

17. A condensation product of lubricating vis cosity obtained by:condensing, at a temperature of about 600 F. for about ten hours andwith a pressure 01' about 200 pounds per square inch, about sixteenmolar proportions of decene-l, about four molar proportions of butadieneand one molar proportion of sulfur.

WILLIAM E. GARWOOD. FRANCIS M. SEGER. ALEXANDER N. SACHANEN.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 2,213,423 Wiezevich Sept. 3, 19402,337,473 Knowles Dec. 21, 1943 2 2,439,610 Morris et a1 Apr. 13, 19482,442,644 Elwell June 1, 1948

1. THE METHOD OF PREPARATION OF A VISCOUS OIL, WHICH COMPRISES:CONDENSING, AT A TEMPERATURE BETWEEN ABOUT 400*F. AND ABOUT 750*F. FOR APERIOD OF TIME FROM ABOUT TEN HOURS TO ABOUT ONE HOUR, RESPECTIVELY, ONEMOLAR PROPORTION OF A STRAIGHT CHAIN, ALPHA MONO-OLEFIN HAVING FROM 5 TO18 CARBON ATOMS PER MOLECULE, FROM ABOUT 0.01 TO ABOUT ONE MOLARPROPORTION OF A CONJUGATED HYDROCARBON AND FROM ABOUT 0.001 TO ABOUT ONEMOLAR PROPORTION OF A SUBSTNACE SELECTED FROM THE GROUP CONSISTING OFSULFUR, SELENIUM AND TELLURIUM; SAID CONJUGATED HYDROCARBON BEINGCHARACTERIZED BY AT LEAST ONE
 14. A VISCOUS OIL COMPOSITION COMPRISING AMINERAL OIL OF LUBRICATING VISCOSITY IN MAJOR PROPORTION AND A MINORPROPORTION, FROM ABOUT ONE TO ABOUT TEN PER CENT, OF A CONDENSATIONPRODUCT; SAID CONDENSANTION PRODUCT BEING OBTAINED BY: CONDENSING, AT ATEMPERATURE BETWEEN ABOUT 400*F. AND ABOUT 750*F. FOR A PERIOD OF TIMEFROM ABOUT TEN HOURS TO ABOUT ONE HOUR, RESPECTIVELY, ONE MOLARPROPORTION OF A STRAIGHT CHAIN, ALPHA MONOOLEFIN HAVING FROM FIVE TOEIGHTEEN CARBON ATOMS PER MOLECULE, FROM ABOUT 0.01 TO ABOUT ONE MOLARPROPORTION OF A CONJUGATED HYDROCARBON AND FROM ABOUR 0.001 TO ABOUT ONEMOLAR PROPORTION OF SULFUR; SAID CONJUGATED HYDROCARBON BEINGCHARACTERIZED BY AT LEAST ONE